Acridinedione as selective flouride ion chemosensor: a detailed spectroscopic and quantum mechanical investigation

Nafees Iqbal; Syed Abid Ali; Iqra Munir; Saima Khan; Khurshid Ayub; Mariya al-Rashida; Muhammad Islam; Zahid Shafiq; Ralf Ludwig; Abdul Hameed

doi:10.1039/C7RA11974G

Acridinedione as selective flouride ion chemosensor: a detailed spectroscopic and quantum mechanical investigation†

Nafees Iqbal,^a Syed Abid Ali,^a Iqra Munir,^a Saima Khan,^b Khurshid Ayub,

^b Mariya al-Rashida,

^c Muhammad Islam,^d Zahid Shafiq,^dg Ralf Ludwig

^ef and Abdul Hameed

*^a

Author affiliations

* Corresponding authors

^a H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan
E-mail: abdul_hameed8@hotmail.com, abdul_hameed@iccs.edu
Fax: +92-21-3481901
Tel: +92-21-99261701-2

^b Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad, KPK, Pakistan 22060

^c Department of Chemistry, Forman Christian College, A Chartered University, Ferozepur Road, Lahore, Pakistan

^d Institute of Chemical Sciences, Bahauddin Zakariya University, Multan, Pakistan

^e Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany

^f Department of Physical Chemistry, University of Rostock, Dr.-Lorenz-Weg 1, 18059 Rostock, Germany

^g Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan

Abstract

The use of small molecules as chemosensors for ion detection is rapidly gaining popularity by virtue of the advantages it offers over traditional ion sensing methods. Herein we have synthesized a series of acridine(1,8)diones (7a–7l) and explored them for their potential to act as chemosensors for the detection of various anions such as fluoride (F⁻), acetate (OAc⁻), bromide (Br⁻), iodide (I⁻), bisulfate (HSO₄⁻), chlorate (ClO₃⁻), perchlorate (ClO₄⁻), cyanide (CN⁻), and thiocyanate (SCN⁻). Acridinediones were found to be highly selective chemosensors for fluoride ions only. To investigate in detail the mechanism of selective fluoride ion sensing, detailed spectroscopic studies were carried out using UV-visible, fluorescence and ¹H NMR spectroscopy. Fluoride mediated (NH) proton abstraction of acridinedione was found to be responsible for the observed selective fluoride ion sensing. Quantum mechanical computational studies, using time dependent density functional theory (TDDFT) were also carried out, whereupon comparison of acridinedione interaction with fluoride and acetate ions explained the acridinedione selectivity for the detection of fluoride anions. Our results provide ample evidence and rationale for further modulation and exploration of acridinediones as non-invasive chemosensors for fluoride ion detection in a variety of sample types.

RSC Advances

Acridinedione as selective flouride ion chemosensor: a detailed spectroscopic and quantum mechanical investigation†

Abstract

Associated articles

Supplementary files

Article information

Download Citation

Permissions

Acridinedione as selective flouride ion chemosensor: a detailed spectroscopic and quantum mechanical investigation

Social activity

Search articles by author

Spotlight

Advertisements